1,4-Dioxane → HCID 178441228, compound

HRID 406280Notes

Reaction equation

HRID 406280 reaction equation
CC([N:5]([C@H:9]1[CH2:12][C@H:11]([O:13][C:14]2[CH:19]=[C:18]([F:20])[C:17]([C:21]([CH3:24])([CH3:23])[CH3:22])=[C:16]([F:25])[CH:15]=2)[CH2:10]1)C(=O)[O-])(C)C.O1CCOCC1>Cl>[CH3:24][C:21]([C:17]1[C:16]([F:25])=[CH:15][C:14]([O:13][C@H:11]2[CH2:10][C@H:9]([NH2:5])[CH2:12]2)=[CH:19][C:18]=1[F:20])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 178441233HCID 178441233, compound

Product 1

HCID 178441228HCID 178441228, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1,1-dimethylethyl(trans-3-{[4-(1,1-dimethylethyl)-3,5-difluorophenyl]oxy}cyclobutyl)carbamate (257 mg, 0.723 mmol) was stirred in 4M HCl in dioxane (5 mL, 20 mmol) overnight and then concentrated in vacuo and loaded onto an SCX cartridge (10 g) and eluted with MeOH (3 column volumes) and then flushed with ammonia in MeOH. Concentration of the product containing fractions in vacuo gave the title compound (142.3 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. washeluted with MeOH (3 column volumes)
  3. customflushed with ammonia in MeOH
  4. additionConcentration of the product containing fractions in vacuo

Sources & evidence

ORD record
ord-77cc67c5070c4109934745d28da33a67
Source dataset
uspto-grants-2014_06
Patent number
US08754101B2

Reaction notes

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